Heterocyclic compound containing heteroatom substituted fluorene and optoelectronic device

ABSTRACT

A heterocyclic compound containing heteroatom substituted fluorene and an optoelectronic device are provided. The heterocyclic compound includes a structure in Formula I:where Y is selected from O or S; at least one of X1, X2, X3, X4, X5, X6, X7 and X8 is a N atom, and rest are CR2; L1, L2, and L3 are independently selected from single bond, substituted or unsubstituted aromatic groups; Ar1 and Ar2 are independently selected from substituted or unsubstituted aromatic groups or heteroaryl groups; R1 is selected from a hydrogen atom, a deuterium atom, or an aromatic group or a heteroaryl group condensed with adjacent groups; and R2 is selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5 alkyl group, a halogen, a cyano group, or an amino group.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the priority of Chinese patent application No.202111452323.0, filed on Nov. 30, 2021, the entirety of which isincorporated herein by reference.

FIELD

The present disclosure generally relates to the field of organicelectroluminescent material technology and, more particularly, relatesto a heterocyclic compound containing heteroatom substituted fluoreneand an optoelectronic device.

BACKGROUND

According to a direction of light emitted by an organic light-emittinglayer, organic light-emitting diode (OLED) display can be divided into abottom-emitting OLED display and a top-emitting OLED display. In thebottom-emitting OLED display, light emits towards a direction facing thesubstrate, a reflective electrode is formed over the organiclight-emitting layer, and a transparent electrode is formed under theorganic light-emitting layer. If the OLED display is an active matrixOLED display, a portion of the thin film transistors formed therein doesnot transmit light, such that a light-emitting area is reduced. On theother hand, in the top-emitting OLED display, the transparent electrodeis formed over the organic light-emitting layer, and the reflectiveelectrode is formed under the organic light-emitting layer, such thatlight emits towards a direction opposite to the substrate, therebyincreasing the light transmission area and improving the brightness.

Currently, a refractive index of an OLED device cannot meet marketdemand, and the light extraction effect is insufficient. The differencein measured refractive indices for respective wavelength regions of theblue light, green light, and red light is substantially large.Therefore, not all the light emitted by the blue, green, and redlight-emitting devices can simultaneously obtain the high lightextraction efficiency.

In view of the low light extraction efficiency of an existing OLEDdevice, a capping layer (CPL), e.g., a light extraction material, needsto be added in the device structure. According to the principles ofoptical absorption and refraction, a refractive index of a material ofthe surface capping layer is as high as possible.

SUMMARY

One aspect of the present disclosure provides a heterocyclic compoundcontaining heteroatom substituted fluorene. The heterocyclic compoundincludes a structure in Formula I:

where Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅, X₆,X₇ and X₈ is a N atom, and rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.

Another aspect of the present disclosure provides a display panel. Thedisplay panel includes an organic light-emitting device. The organiclight-emitting device includes an anode, a cathode, and an organic thinlayer disposed between the anode and the cathode. The cathode is coveredwith a capping layer, and the capping layer includes any one or acombination of at least two of heterocyclic compounds. Each heterocycliccompound includes a structure in Formula I:

where Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅, X₆,X₇ and X₈ is a N atom, and rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.

Another aspect of the present disclosure provides a display device. Thedisplay device includes a display panel. The display panel includes anorganic light-emitting device. The organic light-emitting deviceincludes an anode, a cathode, and an organic thin layer disposed betweenthe anode and the cathode. The cathode is covered with a capping layer,and the capping layer includes any one or a combination of at least twoof heterocyclic compounds. Each heterocyclic compound includes astructure in Formula I:

where Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅, X₆,X₇ and X₈ is a N atom, and rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.

Other aspects of the present disclosure can be understood by thoseskilled in the art in light of the description, the claims, and thedrawings of the present disclosure.

BRIEF DESCRIPTION OF THE DRAWINGS

To more clearly illustrate the embodiments of the present disclosure,the drawings will be briefly described below. The drawings in thefollowing description are certain embodiments of the present disclosure,and other drawings may be obtained by a person of ordinary skill in theart in view of the drawings provided without creative efforts.

FIG. 1 illustrates a schematic diagram of an exemplary organiclight-emitting device consistent with disclosed embodiments of thepresent disclosure.

DETAILED DESCRIPTION OF THE DISCLOSURE

Reference will now be made in detail to exemplary embodiments of thedisclosure, which are illustrated in the accompanying drawings. Whereverpossible, the same reference numbers will be used throughout thedrawings to refer to the same or the alike parts. The describedembodiments are some but not all of the embodiments of the presentdisclosure. Based on the disclosed embodiments, persons of ordinaryskill in the art may derive other embodiments consistent with thepresent disclosure, all of which are within the scope of the presentdisclosure.

Similar reference numbers and letters represent similar terms in thefollowing FIGURES, such that once an item is defined in one FIGURE, itdoes not need to be further discussed in subsequent FIGURES.

The present disclosure provides a heterocyclic compound containingheteroatom substituted fluorene. The heterocyclic compound containingheteroatom substituted fluorene may have a structure shown in Formula I:

where Y may be selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅,X₆, X₇ and X₈ may be a N atom, and the rest may be CR₂; L₁, L₂, and L₃may be independently selected from single bond, substituted orunsubstituted aromatic groups; Ar₁ and Ar₂ may be independently selectedfrom substituted or unsubstituted aromatic groups or heteroaryl groups;R₁ may be selected from a hydrogen atom, a deuterium atom, or anaromatic group or a heteroaryl group condensed with adjacent groups; andR₂ may be selected from a hydrogen atom, a deuterium atom, a substitutedor unsubstituted C1-C5 alkyl group, a halogen, a cyano group, or anamino group.

The present disclosure provides a heterocyclic compound containingheteroatom substituted fluorene and an optoelectronic device. Theprepared heterocyclic compound may have a substantially high refractiveindex in the entire visible light region. The difference in measuredrefractive indices of the heterocyclic compound for respectivewavelength regions of blue light, green light, and red light may besubstantially small, and the light extraction efficiency of theheterocyclic compound in a blue light device, a green light device and ared light device may be substantially high, thereby achieving asubstantially high device efficiency. In the present disclosure, byintroducing heteroatom substituted fluorene in the molecular structure,although the molecular volume change is substantially small, thepolarizability of the molecule may be greatly improved, which maycomprehensively improve the refractive index of the heterocycliccompound in wavelength regions of the blue light, green light, and redlight.

In one embodiment, the substituent of the aromatic group or heteroarylgroup may be selected from a C1-C10 alkyl group or a C1-C10 alkoxygroup.

In one embodiment, any one, two or three of X₁, X₂, X₃, X₄, X₅, X₆, X₇,and X₈ may be a N atom, and the rest may be CR₂.

In one embodiment, the R₂ may be a hydrogen atom, a deuterium atom, F,Cl, Br, a cyano group, or a trifluoromethyl group.

In one embodiment, the heteroatom substituted fluorene in Formula I mayhave any one of the following structures:

where Y may be selected from O or S, and the above structure may beconnected to L₁ through any carbon atom.

In one embodiment, the heteroatom substituted fluorene in Formula I mayhave any one of the following structures:

where Y may be selected from O or S, and the above structure may beconnected to L₁ through any carbon atom.

In one embodiment, the heteroatom substituted fluorene in Formula I mayhave any one of the following structures:

where Y may be selected from O or S, and the above structure may beconnected to L₁ through any carbon atom.

In one embodiment, the heteroatom substituted fluorene in Formula I mayhave any one of the following structures:

where Y may be selected from O or S, and the above structure may beconnected to L₁ through any carbon atom.

The above heteroatom substituted fluorene may refer to the followingstructure in the structural formula:

In one embodiment, the heterocyclic compound may have any one of thefollowing structures:

In one embodiment, the L₁, L₂, and L₃ may be independently selected fromsingle bond, substituted or unsubstituted aromatic groups. Thesubstituent of the aromatic group may be selected from deuterium atom.

In one embodiment, the L₁, L₂, and L₃ may be independently selected fromphenylene, biphenylene, terphenylene, naphthylene, anthrylene,phenanthrylene, pyrenylene, fluoranthene, triphenylene or fluorenylene.

In one embodiment, the L₁, L₂, and L₃ may be independently selected fromany one of the following structures:

where # may represent a connection position.

In one embodiment, the Ar₁ and Ar₂ may be independently selected fromsubstituted or unsubstituted aromatic groups or heteroaryl groups. Thesubstituent of the aforementioned aromatic group or heteroaryl group maybe selected from a deuterium atom.

In one embodiment, the Ar₁ and Ar₂ may be independently selected fromsubstituted or unsubstituted condensed aromatic groups or condensedheteroaryl groups. The substituent of the aforementioned condensedaromatic group or condensed heteroaryl group may be selected from adeuterium atom.

In one embodiment, the Ar₁ and Ar₂ may be independently selected fromphenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl,pyrenyl, fluoranthene, triphenylene, fluorenyl, pyrrolyl, furyl,thienyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, benzofuranyl,benzothienyl, dibenzofuranyl, dibenzothienyl, oxazolyl, oxadiazolyl,thiazolyl, thiadiazolyl, benzoxazolyl, benzothiazolyl, imidazolyl,pyrazolyl, indolyl, quinolinyl, isoquinolinyl, purinyl, isoxazolyl,isothiazole, pyrone, pyrazinyl, thienofuranyl, thienopyrrolyl,pyrrolopyridyl, pyridopyrimidinyl, pyrazolooxazolyl,pyrazinopyridazinyl, imidazothiazolyl or coumarin.

In one embodiment, the Ar₁ and Ar₂ may be independently selected fromany one of the following structures:

where # may represent a connection position.

In one embodiment, the heterocyclic compound may have any one of thefollowing structures:

The above disclosed heterocyclic compound in the present disclosure maybe prepared by the existing method, and those skilled in the art mayselect a specific synthesis method according to conventional technicalknowledge. The present disclosure may merely provide an exemplarysynthesis route, which may not be limited by the present disclosure.

A representative synthetic route of the compound shown in Formula I inthe present disclosure may include following:

In one embodiment, the above-disclosed compound in the presentdisclosure may be applied to the CPL layer of a top-emitting OLEDdevice. In another embodiment, the above-disclosed compound may be usedas an optical auxiliary layer such as a hole transport layer, anelectron blocking layer, etc.

The present disclosure also provides a display panel including anorganic light-emitting device. The organic light-emitting device mayinclude an anode, a cathode, and an organic thin layer disposed betweenthe anode and the cathode. The cathode may be covered with a cappinglayer, and the capping layer may include any one or a combination of atleast two of the above-disclosed heterocyclic compounds.

The present disclosure also provides a display panel including anorganic light-emitting device. The organic light-emitting device mayinclude an anode, a cathode, and an organic thin layer disposed betweenthe anode and the cathode. The organic thin layer may include a holetransport layer, and the hole transport layer may include any one or acombination of at least two of the above-disclosed heterocycliccompounds.

The present disclosure also provides a display panel including anorganic light-emitting device. The organic light-emitting device mayinclude an anode, a cathode, and an organic thin layer disposed betweenthe anode and the cathode. The organic thin layer may include anelectron blocking layer, and the electron blocking layer may include anyone or a combination of at least two of the above-disclosed heterocycliccompounds.

The organic light-emitting device in the present disclosure may includea substrate, an indium-tin oxide (ITO) anode, a first hole transportlayer, a second hole transport layer, an electron blocking layer, alight-emitting layer, a first electron transport layer, a secondelectron transport layer, a cathode (Mg—Ag electrode, a mass ratio of Mgover Ag may be approximately 1:9), and a capping layer (CPL) that arestacked in sequence.

In one embodiment, the anode material of the organic light-emittingdevice may be selected from a metal, a metal oxide, and a conductivepolymer. The metal may include copper, gold, silver, iron, chromium,nickel, manganese, palladium, and platinum, or an alloy thereof, etc.The metal oxide may include indium oxide, zinc oxide, indium-tin oxide(ITO), indium-zinc oxide (IZO), etc. The conductive polymer may includepolyaniline, polypyrrole, poly(3-methylthiophene), etc. In addition tothe above materials and combinations that facilitate the hole injection,the anode material may further include any other suitable material.

In one embodiment, the cathode material of the organic light-emittingdevice may be selected from a metal, and a multilayer metal material.The metal may include aluminum, magnesium, silver, indium, tin,titanium, or an alloy thereof, etc. The multilayer metal material mayinclude LiF/Al, LiO₂/Al, BaF₂/Al, etc. In addition to the abovematerials and combinations that facilitate electron injection, thecathode material may further include any other suitable material.

In one embodiment, the organic thin layer of the organic light-emittingdevice may include at least one light-emitting layer (EML), and mayfurther include other functional layers, including a hole injectionlayer (HIL), a hole transport layer (HTL), an electron blocking layer(EBL), a hole blocking layer (HBL), an electron transport layer (ETL),and an electron injection layer (EIL).

In one embodiment, the organic light-emitting device may be preparedaccording to the following method. An anode may be formed on atransparent or an opaque smooth substrate, an organic thin layer may beformed on the anode, and a cathode may be formed on the organic thinlayer.

In one embodiment, forming the organic thin layer may includeevaporation, sputtering, spin coating, dipping, ion plating, or anyother known film formation method.

The present disclosure also provides a display device including theabove-disclosed display panel.

In the present disclosure, an organic light-emitting device (OLEDdevice) may be applied to the display device. The organic light-emittingdisplay device may include a mobile phone display, a computer display, aTV display, a smart watch display, a smart car display panel, VR or ARhelmet display, or display of various smart devices, etc.

Exemplary Embodiment 1

A synthetic route of compound M001 and detailed preparation method mayinclude following:

(1) The M001-1 (0.5 mmol), M001-2 (0.75 mmol), K₂CO₃ (0.5 mmol), PdCl₂(5×10⁴ mmol), TPPDA (5×10⁴ mmol) may be added into 3 mL o-xylenesolution and then may be mixed. The mixed solution may be loaded into a50 mL flask, and may react at 100° C. for 24 hours. After cooling toroom temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM001-3 may be obtained through column chromatography.

(2) M001-3 (0.5 mmol), M001-4 (1.5 mmol), KO(t-Bu) (0.75 mmol),[Pd(cinnamyl)Cl]₂ (2 mol %), Ligand (1.5 mol %) may be added into 3 mLtoluene solution and then may be mixed. The mixed solution may be loadedinto a 50 mL flask, and may react at 110° C. for 12 hours. After coolingto room temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM001 may be obtained through column chromatography.

Through the matrix-assisted laser desorption/ionization time-of-flightmass spectrometry (MALDI-TOF MS (m/z)), the structure of the targetproduct M001 may be obtained as C₄₇H₃₀N₄O with a calculated value of666.2 and a test value of 666.1.

Elemental analysis: theoretical value C, 84.66, H, 4.54, N, 8.40; testvalue C, 84.66, H, 4.53, N, 8.40.

Exemplary Embodiment 2

A synthetic route of compound M029 and detailed preparation method mayinclude following:

(1) M001-3 (0.5 mmol), M029-1 (1.5 mmol), KO(t-Bu) (0.75 mmol),[Pd(cinnamyl)Cl]₂ (2 mol %), Ligand (1.5 mol %) may be added into 3 mLtoluene solution and then may be mixed. The mixed solution may be loadedinto a 50 mL flask, and may react at 110° C. for 12 hours. After coolingto room temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM029 may be obtained through column chromatography.

Through the matrix-assisted laser desorption/ionization time-of-flightmass spectrometry (MALDI-TOF MS (m/z)), the structure of the targetproduct M029 may be obtained as C₄₃H₂₆N₄O₃ with a calculated value of646.2 and a test value of 646.3.

Elemental analysis: theoretical value C, 79.86, H, 4.05, N, 8.66; testvalue C, 79.87, H, 4.05, N, 8.66.

Exemplary Embodiment 3

A synthetic route of compound M039 and detailed preparation method mayinclude following:

(1) M001-3 (0.5 mmol), M039-1 (1.5 mmol), KO(t-Bu) (0.75 mmol),[Pd(cinnamyl)Cl]₂ (2 mol %), Ligand (1.5 mol %) may be added into 3 mLtoluene solution and then may be mixed. The mixed solution may be loadedinto a 50 mL flask, and may react at 110° C. for 12 hours. After coolingto room temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM039 may be obtained through column chromatography.

Through the matrix-assisted laser desorption/ionization time-of-flightmass spectrometry (MALDI-TOF MS (m/z)), the structure of the targetproduct M039 may be obtained as C₄₉H₃₂N₂O with a calculated value of664.2 and a test value of 664.3.

Elemental analysis: theoretical value C, 88.53, H, 4.85, N, 4.21; testvalue C, 88.53, H, 4.86, N, 4.21.

Exemplary Embodiment 4

A synthetic route of compound M265 and detailed preparation method mayinclude following:

(1) The M265-1 (0.5 mmol), M001-2 (0.75 mmol), K₂CO₃ (0.5 mmol), PdCl₂(5×10⁴ mmol), TPPDA (5×10⁴ mmol) may be added into 3 mL o-xylenesolution and then may be mixed. The mixed solution may be loaded into a50 mL flask, and may react at 100° C. for 24 hours. After cooling toroom temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM265-2 may be obtained through column chromatography.

(2) M265-2 (0.5 mmol), M029-1 (1.5 mmol), KO(t-Bu) (0.75 mmol),[Pd(cinnamyl)Cl]₂ (2 mol %), Ligand (1.5 mol %) may be added into 3 mLtoluene solution and then may be mixed. The mixed solution may be loadedinto a 50 mL flask, and may react at 110° C. for 12 hours. After coolingto room temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM265 may be obtained through column chromatography.

Through the matrix-assisted laser desorption/ionization time-of-flightmass spectrometry (MALDI-TOF MS (m/z)), the structure of the targetproduct M265 may be obtained as C₄₂H₂₅N₅O₂S with a calculated value of663.2 and a test value of 663.1.

Elemental analysis: theoretical value C, 76.00, H, 3.80, N, 10.55; testvalue C, 76.01, H, 3.80, N, 10.55.

Exemplary Embodiment 5

A synthetic route of compound M382 and detailed preparation method mayinclude following:

(1) The M001-1 (0.5 mmol), M382-1 (0.75 mmol), K₂CO₃ (0.5 mmol), PdCl₂(5×10⁴ mmol), TPPDA (5×10⁴ mmol) may be added into 3 mL o-xylenesolution and then may be mixed. The mixed solution may be loaded into a50 mL flask, and may react at 100° C. for 24 hours. After cooling toroom temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM382-2 may be obtained through column chromatography.

(2) The M382-2 (0.5 mmol), M382-3 (1.5 mmol), KO(t-Bu) (0.75 mmol),[Pd(cinnamyl)Cl]₂ (2 mol %), Ligand (1.5 mol %) may be added into 3 mLtoluene solution and then may be mixed. The mixed solution may be loadedinto a 50 mL flask, and may react at 110° C. for 12 hours. After coolingto room temperature, saturated MgSO₄ aqueous and ethyl acetate may beslowly added into the mixed solution for extraction three times. Then,solvent may be removed through a rotary evaporator, and a crude productM382 may be obtained through column chromatography.

Through the matrix-assisted laser desorption/ionization time-of-flightmass spectrometry (MALDI-TOF MS (m/z)), the structure of the targetproduct M382 may be obtained as C₄₇H₂₈N₄OS₂ with a calculated value of728.2 and a test value of 728.1.

Elemental analysis: theoretical value C, 77.45, H, 3.87, N, 7.69; testvalue C, 77.44,

The preparation method of the disclosed compounds in the presentdisclosure used in the specific embodiments may be similar to theabove-mentioned method, and may not be repeated herein. Thecharacterization results, such as the results of mass spectrometry andelemental analysis, may be provided and shown in Table 1.

TABLE 1 Mass Elemental spectrometry results analysis results CalculatedTest Theoretical Test Compound value value value value M002 666.2 666.1C, 84.66; H, 4.54; N, 8.40; C, 84.66; H, 4.56; N, 8.40; M008 668.2 668.1C, 80.82; H, 4.22; N, 12.57; C, 80.80; H, 4.22; N, 12.58; M011 668.2668.0 C, 80.82; H, 4.22; N, 12.57; C, 80.82; H, 4.22; N, 12.56; M016668.1 668.2 C, 80.82; H, 4.22; N, 12.57; C, 80.82; H, 4.23; N, 12.57;M021 668.2 668.1 C, 80.82; H, 4.22; N, 12.57; C, 80.83; H, 4.22; N,12.57; M024 668.2 668.0 C, 80.82; H, 4.22; N, 12.57; C, 80.82; H, 4.22;N, 12.56; M025 668.2 668.3 C, 80.82; H, 4.22; N, 12.57; C, 80.82; H,4.23; N, 12.57; M032 744.2 744.1 C, 85.46; H, 4.33; N, 3.76; C, 85.47;H, 4.32; N, 3.76; M033 776.2 776.1 C, 81.93; H, 4.15; N, 3.61; C, 81.94;H, 4.15; N, 3.61; M035 746.2 746.1 C, 82.02; H, 4.05; N, 7.50; C, 82.02;H, 4.05; N, 7.51; M036 746.2 746.3 C, 82.02; H, 4.05; N, 7.50; C, 82.02;H, 4.06; N, 7.51; M037 764.3 764.2 C, 89.50; H, 4.74; N, 3.66; C, 89.51;H, 4.74; N, 3.66; M038 864.3 864.2 C, 90.25; H, 4.66; N, 3.24; C, 90.25;H, 4.67; N, 3.24; M042 716.3 716.1 C, 85.45; H, 4.50; N, 7.82; C, 85.44;H, 4.50; N, 7.82; M045 716.3 716.1 C, 85.45; H, 4.50; N, 7.82; C, 85.45;H, 4.51; N, 7.82; M048 718.3 718.2 C, 81.88; H, 4.21; N, 11.69; C,81.89; H, 4.21; N, 11.69; M056 718.3 718.2 C, 81.88; H, 4.21; N, 11.69;C, 81.88; H, 4.20; N, 11.69; M063 718.3 718.4 C, 81.88; H, 4.21; N,11.69; C, 81.89; H, 4.20; N, 11.68; M065 746.2 746.3 C, 82.02; H, 4.05;N, 7.50; C, 82.03; H, 4.06; N, 7.50; M068 844.3 844.2 C, 86.71; H, 4.29;N, 3.32; C, 86.71; H, 4.28; N, 3.33; M072 846.3 846.2 C, 83.67; H, 4.05;N, 6.62; C, 83.68; H, 4.05; N, 6.62; M078 764.3 764.1 C, 89.50; H, 4.74;N, 3.66; C, 89.51; H, 4.74; N, 3.66; M081 666.2 666.0 C, 84.66; H, 4.54;N, 8.40; C, 84.66; H, 4.55; N, 8.40; M086 666.2 666.0 C, 84.66; H, 4.54;N, 8.40; C, 84.65; H, 4.55; N, 8.40; M088 668.2 668.1 C, 80.82; H, 4.22;N, 12.57; C, 80.82; H, 4.23; N, 12.57; M092 668.2 668.0 C, 80.82; H,4.22; N, 12.57; C, 80.81; H, 4.22; N, 12.57; M104 668.2 668.0 C, 80.82;H, 4.22; N, 12.57; C, 80.82; H, 4.22; N, 12.58; M105 646.2 646.1 C,79.86; H, 4.05; N, 8.66; C, 79.85; H, 4.05; N, 8.67; M113 764.3 764.2 C,89.50; H, 4.74; N, 3.66; C, 89.50; H, 4.75; N, 3.66; M123 716.3 716.3 C,85.45; H, 4.50; N, 7.82; C, 85.45; H, 4.51; N, 7.82; M128 718.3 718.2 C,81.88; H, 4.21; N, 11.69; C, 81.88; H, 4.21; N, 11.69; M136 718.3 718.1C, 81.88; H, 4.21; N, 11.69; C, 81.88; H, 4.20; N, 11.69; M143 768.3768.2 C, 82.79; H, 4.20; N, 10.93; C, 82.79; H, 4.21; N, 10.93; M145746.2 746.1 C, 82.02; H, 4.05; N, 7.50; C, 82.02; H, 4.04; N, 7.50; M158764.3 764.2 C, 89.50; H, 4.74; N, 3.66; C, 89.51; H, 4.74; N, 3.66; M161666.2 666.3 C, 84.66; H, 4.54; N, 8.40; C, 84.66; H, 4.54; N, 8.41; M163666.2 666.3 C, 84.66; H, 4.54; N, 8.40; C, 84.66; H, 4.55; N, 8.41; M167666.2 666.3 C, 84.66; H, 4.54; N, 8.40; C, 84.64; H, 4.56; N, 8.41; M171668.2 668.1 C, 80.82; H, 4.22; N, 12.57; C, 80.82; H, 4.23; N, 12.58;M184 668.2 668.1 C, 80.82; H, 4.22; N, 12.57; C, 80.83; H, 4.22; N,12.57; M189 646.2 646.1 C, 79.86; H, 4.05; N, 8.66; C, 79.86; H, 4.04;N, 8.66; M192 744.2 744.1 C, 85.46; H, 4.33; N, 3.76; C, 85.46; H, 4.33;N, 3.77; M197 764.3 764.2 C, 89.50; H, 4.74; N, 3.66; C, 89.50; H, 4.75;N, 3.66; M198 864.3 864.2 C, 90.25; H, 4.66; N, 3.24; C, 90.25; H, 4.67;N, 3.24; M215 743.2 743.1 C, 80.74; H, 3.93; N, 13.18; C, 80.74; H,3.93; N, 13.17; M220 786.2 786.2 C, 76.33; H, 3.72; N, 10.68; C, 76.33;H, 3.72; N, 10.69; M228 769.3 769.2 C, 81.13; H, 4.06; N, 12.74; C,81.13; H, 4.07; N, 12.74; M229 747.2 747.1 C, 80.31; H, 3.91; N, 9.37;C, 80.31; H, 3.90; N, 9.37; M237 865.3 865.2 C, 88.76; H, 4.54; N, 4.85;C, 88.76; H, 4.55; N, 4.85; M242 765.3 765.2 C, 87.82; H, 4.61; N, 5.49;C, 87.83; H, 4.61; N, 5.49; M246 683.2 683.1 C, 80.79; H, 4.27; N,10.24; C, 80.79; H, 4.28; N, 10.24; M261 685.2 685.1 C, 77.06; H, 3.97;N, 14.30; C, 77.06; H, 3.98; N, 14.30; M274 696.1 696.2 C, 70.66; H,3.47; N, 12.06; C, 70.66; H, 3.48; N, 12.06; M277 782.3 782.2 C, 84.37;H, 4.38; N, 7.16; C, 84.37; H, 4.39; N, 7.16; M295 735.2 735.1 C, 78.35;H, 3.97; N, 13.32; C, 78.36; H, 3.96; N, 13.32; M305 663.2 663.1 C,76.00; H, 3.80; N, 10.55; C, 76.01; H, 3.80; N, 10.56; M314 682.2 682.1C, 82.67; H, 4.43; N, 8.21; C, 82.67; H, 4.45; N, 8.21; M324 760.2 760.1C, 83.66; H, 4.24; N, 3.68; C, 83.66; H, 4.24; N, 3.69; M340 684.2 684.1C, 78.92; H, 4.12; N, 12.27; C, 78.90; H, 4.12; N, 12.28; M353 662.2662.1 C, 77.93; H, 3.95; N, 8.45; C, 77.93; H, 3.96; N, 8.45; M362 880.3880.1 C, 88.61; H, 4.58; N, 3.18; C, 88.62; H, 4.57; N, 3.18; M381 696.2696.1 C, 81.02; H, 4.05; N, 8.04; C, 81.02; H, 4.06; N, 8.04; M385 696.2696.1 C, 81.02; H, 4.05; N, 8.04; C, 81.03; H, 4.05; N, 8.03; M388 796.3796.2 C, 86.13; H, 4.31; N, 3.52; C, 86.13; H, 4.30; N, 3.52; M400 685.2685.1 C, 77.06; H, 3.97; N, 14.30; C, 77.06; H, 3.98; N, 14.30; M401716.3 716.2 C, 85.45; H, 4.50; N, 7.82; C, 85.45; H, 4.51; N, 7.82; M413712.2 712.3 C, 79.19; H, 3.96; N, 7.86; C, 79.19; H, 3.97; N, 7.86; M416810.2 810.3 C, 84.42; H, 4.23; N, 3.45; C, 84.42; H, 4.22; N, 3.45;

The refractive indices of the compounds may be detected, and the resultsmay be shown in Table 2.

TABLE 2 Refractive Refractive Refractive index index index No. Structure460 nm 530 nm 620 nm M001

2.29 2.14 2.06 M002

2.30 2.15 2.07 M008

2.34 2.18 2.08 M011

2.28 2.13 2.05 M016

2.29 2.14 2.06 M021

2.18 2.07 2.00 M024

2.18 2.07 2.00 M025

2.22 2.10 2.03 M029

2.26 2.12 2.04 M032

2.24 2.12 2.05 M033

2.24 2.12 2.05 M035

2.38 2.21 2.11 M036

2.25 2.12 2.05 M037

2.29 2.16 2.08 M038

2.26 2.14 2.06 M039

2.19 2.07 2.00 M042

2.36 2.20 2.11 M045

2.24 2.12 2.05 M048

2.40 2.23 2.12 M056

2.35 2.19 2.10 M063

2.32 2.18 2.10 M065

2.38 2.21 2.11 M068

2.36 2.21 2.12 M072

2.37 2.21 2.12 M078

2.34 2.19 2.11 M081

2.18 2.09 2.02 M086

2.09 2.03 1.98 M088

2.23 2.13 2.04 M092

2.17 2.08 2.02 M104

2.13 2.04 1.98 M105

2.15 2.04 1.98 M113

2.12 2.03 1.98 M123

2.16 2.07 2.01 M128

2.32 2.18 2.09 M136

2.30 2.16 2.07 M143

2.22 2.13 2.06 M145

2.26 2.13 2.05 M158

2.25 2.12 2.06 M161

2.27 2.13 2.06 M163

2.22 2.11 2.03 M167

2.20 2.10 2.02 M171

2.26 2.12 2.04 M184

2.16 2.06 2.00 M189

2.24 2.12 2.04 M192

2.22 2.12 2.05 M197

2.23 2.12 2.05 M198

2.20 2.10 2.03 M215

2.22 2.10 2.03 M220

2.16 2.05 1.98 M228

2.17 2.08 2.02 M229

2.26 2.12 2.05 M237

2.30 2.18 2.10 M242

2.26 2.14 2.07 M246

2.17 2.05 2.00 M261

2.09 2.00 1.96 M265

2.13 2.02 1.97 M274

2.24 2.10 2.03 M277

2.22 2.11 2.04 M295

2.27 2.13 2.05 M305

2.18 2.06 1.99 M314

2.07 1.99 1.95 M324

2.11 2.02 1.97 M340

2.28 2.14 2.06 M353

2.26 2.12 2.04 M362

2.32 2.19 2.11 M381

2.33 2.18 2.08 M382

2.38 2.21 2.11 M385

2.31 2.16 2.08 M388

2.29 2.16 2.08 M401

2.14 2.04 1.98 M413

2.10 2.01 1.96 M416

2.10 2.02 1.97 Ref 1

2.03 1.95 1.90 Ref 2

2.21 2.10 2.03 Ref 3

2.20 2.08 2.01 Ref 4

2.18 2.08 2.02

According to the data in Table 1, compared with a commonly used cappinglayer material Ref 1 in the industry, the compounds in the presentdisclosure may have higher refractive indices in the entire visiblewavelength range. Therefore, when the above compounds are used ascapping layer materials in an OLED device of the blue, green and redlight-emitting devices, a substantially high light-emitting efficiencymay be expected.

Application Embodiment 1A

The present application embodiment provides an OLED device. FIG. 1illustrates a schematic diagram of an organic light-emitting deviceconsistent with various disclosed embodiments of the present disclosure.Referring to FIG. 1 , the OLED device may include a substrate 1, ananode 2, a hole injection layer 3, a first hole transport layer 4, asecond hole transport layer 5, a light-emitting layer 6, an electrontransport layer 7, an electron injection layer 8, a cathode 9 and acapping layer 10 that are stacked in sequence.

The structure of the OLED blue-light device may include: ITO (10nm)/compound 1:compound 2 (3:97 mass ratio) (5 nm)/compound 3 (100nm)/compound 4 (5 nm)/compound 5:compound 6 (97:3 mass ratio) (30nm)/compound 7 (5 nm)/compound 8:compound 9 (1:1 mass ratio) (30nm)/Mg:Ag (10:90 mass ratio) (10 nm)/M001 (70 nm).

The preparation method of the OLED device may include following.

1) A glass substrate having a size of 50 mm×50 mm×0.7 mm may beprovided. The glass substrate may be sonicated in isopropanol anddeionized water for 30 minutes, respectively, and then may be exposed toozone for approximately 10 minutes for cleaning, to obtain the substrate1. The obtained glass substrate with a 10 nm indium tin oxide (ITO)anode may be mounted on a vacuum deposition apparatus.

2) The hole injection layer material compound 2 and the p-doped materialcompound 1 may be co-evaporated on the ITO anode 2 through a vacuumevaporation, to form the hole injection layer 3 with a doping ratio ofapproximately 3% (mass ratio) and a thickness of approximately 5 nm.

3) The hole transport layer material compound 3 may be evaporated on thehole injection layer 3 through a vacuum evaporation, to form the firsthole transport layer 4 with a thickness of approximately 100 nm.

4) The hole transport layer material compound 4 may be evaporated on thefirst hole transport layer 4 through a vacuum evaporation, to form thesecond hole transport layer 5 with a thickness of approximately 5 nm.

5) The compound 5 as a host material and the compound 6 as a dopingmaterial may be co-evaporated on the second hole transport layer 5through a vacuum evaporation, to form the light-emitting layer 6 with adoping ratio of approximately 3% (mass ratio) and a thickness ofapproximately 30 nm.

6) The electron transport material compound 7 may be evaporated on thelight-emitting layer 6 through a vacuum evaporation, to form theelectron transport layer 7 with a thickness of approximately 5 nm.

7) The electron transport material compound 8 and the compound 9 may beco-evaporated on the electron transport layer 7 through a vacuumevaporation, to form the electron injection layer 8 with a doping massratio of approximately 1:1 and a thickness of approximately 30 nm.

8) Magnesium-silver electrode may be evaporated on the electroninjection layer 8 through a vacuum evaporation, to form the cathode 9with a Mg:Ag mass ratio of approximately 1:9 and a thickness ofapproximately 10 nm.

9) The compound M001 may be evaporated on the cathode 9 through a vacuumevaporation, to form the capping layer 10 with a thickness ofapproximately 70 nm.

The structure of the compounds used in the OLED device may have thefollowing structures.

Application Embodiment 1B

The present application embodiment provides an OLED device. Thepreparation method of the OLED device in the present applicationembodiment may be the same as the preparation method of the OLED devicein the application embodiment 1A, while the OLED device in the presentembodiment may have the following device structure.

The structure of the OLED green-light device may include: ITO (10nm)/compound 1: compound 2 (3:97 mass ratio) (5 nm)/compound 3 (140nm)/compound 4 (5 nm)/CBP:Ir (ppy)₃ (9:1 mass ratio) (40 nm)/compound 7(5 nm)/compound 8:compound 9 (1:1 mass ratio) (30 nm)/Mg:Ag (10:90 massratio) (10 nm)/M001 (70 nm).

Application Embodiment 1C

The present application embodiment provides an OLED device. Thepreparation method of the OLED device in the present applicationembodiment may be the same as the preparation method of the OLED devicein the application embodiment 1A, while the OLED device in the presentembodiment may have the following device structure.

The structure of the OLED red-light device may include: ITO (10nm)/compound 1: compound 2 (3:97 mass ratio) (5 nm)/compound 3 (190nm)/compound 4 (5 nm)/CBP: Ir(piq)₂(acac) (96:4 mass ratio) (40nm)/compound 7 (5 nm)/compound 8:compound 9 (1:1 mass ratio) (30nm)/Mg:Ag (10:90 mass ratio) (10 nm)/M001 (70 nm).

The difference between application embodiments 2 (A,B,C)-72 (A,B,C) andapplication embodiments 1(A,B,C) may include that the compound M001 maybe replaced with the compounds in Table 3.

Comparative Embodiment 1

The difference between the present comparative embodiment andapplication embodiments 1(A,B,C) may include that the organic compoundM001 in step (9) may be replaced with an equivalent amount of thecomparative compound Ref 1. The other preparation steps in the presentcomparative embodiment may be the same as the preparation steps in theapplication embodiment 1A.

Comparative Embodiment 2

The difference between the present comparative embodiment andapplication embodiments 1(A,B,C) may include that the organic compoundM001 in step (9) may be replaced with an equivalent amount of thecomparative compound Ref 2. The other preparation steps in the presentcomparative embodiment may be the same as the preparation steps in theapplication embodiment 1A.

Comparative Embodiment 3

The difference between the present comparative embodiment andapplication embodiments 1(A,B,C) may include that the organic compoundM001 in step (9) may be replaced with an equivalent amount of thecomparative compound Ref 3. The other preparation steps in the presentcomparative embodiment may be the same as the preparation steps in theapplication embodiment 1A.

Comparative Embodiment 4

The difference between the present comparative embodiment andapplication embodiments 1(A,B,C) may include that the organic compoundM001 in step (9) may be replaced with an equivalent amount of thecomparative compound Ref 4. The other preparation steps in the presentcomparative embodiment may be the same as the preparation steps in theapplication embodiment 1A.

Performance evaluation of the OLED device

A Keithley 2365A digital nano-voltmeter may be used to test the currentof the OLED device at a different voltage, and then the current may bedivided by the light-emitting area to obtain a current density of theOLED device at the different voltage. The brightness and radiant energyflux density of the OLED device at the different voltage may be testedusing a Konicaminolta CS-2000 spectroradiometer. According to thecurrent density and brightness of the OLED device at the differentvoltage, the operating driving voltage and current efficiency (Cd/A)under a same current density (10 mA/cm²) may be obtained. The servicelifetime of the OLED device may be obtained by measuring the durationwhen the brightness of the OLED device reaches 95% of the initialbrightness (under a test condition of 50 mA/cm²). The specific data maybe shown in Table 3.

TABLE 3 Device performance data sheet Blue-light current Green-lightcurrent Red-light current efficiency (based efficiency (based efficiency(based CPL on Comparative on Comparative on Comparative No. materialEmbodiment 1A) Embodiment 1B) Embodiment 1C) Application M001 106% 112%112% Embodiment 1A/1B/1C Application M002 106% 113% 113% Embodiment2A/2B/2C Application M008 107% 114% 113% Embodiment 3A/3B/3C ApplicationM011 106% 111% 110% Embodiment 4A/4B/4C Application M016 106% 111% 111%Embodiment 5A/5B/5C Application M021 104% 107% 108% Embodiment 6A/6B/6CApplication M024 104% 108% 107% Embodiment 7A/7B/7C Application M025105% 109% 109% Embodiment 8A/8B/8C Application M029 106% 110% 110%Embodiment 9A/9B/9C Application M032 106% 111% 110% Embodiment10A/10B/10C Application M033 106% 110% 111% Embodiment 11A/11B/11CApplication M035 107% 114% 114% Embodiment 12A/12B/12C Application M036106% 110% 112% Embodiment 13A/13B/13C Application M037 106% 112% 113%Embodiment 14A/14B/14C Application M038 106% 111% 112% Embodiment15A/15B/15C Application M039 105% 108% 108% Embodiment 16A/16B/16CApplication M042 107% 113% 114% Embodiment 17A/17B/17C Application M045106% 111% 112% Embodiment 18A/18B/18C Application M048 107% 115% 115%Embodiment 19A/19B/19C Application M056 107% 113% 113% Embodiment20A/20B/20C Application M063 107% 114% 114% Embodiment 21A/21B/21CApplication M065 107% 113% 114% Embodiment 22A/22B/22C Application M068107% 113% 115% Embodiment 23A/23B/23C Application M072 107% 114% 115%Embodiment 24A/24B/24C Application M078 107% 113% 114% Embodiment25A/25B/25C Application M081 105% 110% 109% Embodiment 26A/26B/26CApplication M086 104% 107% 106% Embodiment 27A/27B/27C Application M088106% 112% 111% Embodiment 28A/28B/28C Application M092 105% 109% 110%Embodiment 29A/29B/29C Application M104 105% 109% 107% Embodiment30A/30B/30C Application M105 105% 108% 107% Embodiment 31A/31B/31CApplication M113 104% 107% 107% Embodiment 32A/32B/32C Application M123105% 109% 110% Embodiment 33A/33B/33C Application M128 107% 113% 114%Embodiment 34A/34B/34C Application M136 106% 113% 112% Embodiment35A/35B/35C Application M143 106% 112% 111% Embodiment 36A/36B/36CApplication M145 106% 111% 112% Embodiment 37A/37B/37C Application M158106% 111% 112% Embodiment 38A/38B/38C Application M161 106% 112% 111%Embodiment 39A/39B/39C Application M163 106% 111% 110% Embodiment40A/40B/40C Application M167 105% 110% 110% Embodiment 41A/41B/41CApplication M171 106% 112% 111% Embodiment 42A/42B/42C Application M184105% 109% 110% Embodiment 43A/43B/43C Application M189 106% 111% 112%Embodiment 44A/44B/44C Application M192 106% 111% 112% Embodiment45A/45B/45C Application M197 106% 112% 112% Embodiment 46A/46B/46CApplication M198 105% 111% 110% Embodiment 47A/47B/47C Application M215106% 111% 110% Embodiment 48A/48B/48C Application M220 105% 108% 107%Embodiment 49A/49B/49C Application M228 105% 109% 110% Embodiment50A/50B/50C Application M229 106% 112% 111% Embodiment 51A/51B/51CApplication M237 106% 113% 113% Embodiment 52A/52B/52C Application M242106% 111% 112% Embodiment 53A/53B/53C Application M246 105% 109% 107%Embodiment 54A/54B/54C Application M261 104% 106% 105% Embodiment55A/55B/55C Application M265 104% 106% 105% Embodiment 56A/56B/56CApplication M274 106% 110% 109% Embodiment 57A/57B/57C Application M277105% 109% 109% Embodiment 58A/58B/58C Application M295 106% 111% 112%Embodiment 59A/59B/59C Application M305 105% 109% 107% Embodiment60A/60B/60C Application M314 104% 106% 105% Embodiment 61A/61B/61CApplication M324 104% 106% 106% Embodiment 62A/62B/62C Application M340106% 112% 112% Embodiment 63A/63B/63C Application M353 106% 111% 110%Embodiment 64A/64B/64C Application M362 107% 113% 114% Embodiment65A/65B/65C Application M381 107% 113% 113% Embodiment 66A/66B/66CApplication M382 107% 113% 114% Embodiment 67A/67B/67C Application M385107% 113% 114% Embodiment 68A/68B/68C Application M388 106% 114% 113%Embodiment 69A/69B/69C Application M401 104% 106% 105% Embodiment70A/70B/70C Application M413 104% 106% 106% Embodiment 71A/71B/71CApplication M416 104% 106% 106% Embodiment 72A/72B/72C Comparative Ref100% 100% 100% Embodiment 1A/1B/1C Comparative Ref 2 105% 109% 109%Embodiment 2A/2B/2C Comparative Ref 3 105% 108% 108% Embodiment 3A/3B/3CComparative Ref 4 105% 109% 109% Embodiment 4A/4B/4C

As can be seen from the above-disclosed embodiments and comparativeembodiments, compared with the conventional commercial capping layermaterial compound Ref1, the compounds in the present disclosure mayrealize substantially high luminescence when being applied toblue-light, green-light and red-light devices. The light-emittingefficiency of blue-light device is increased by 4%-7%, thelight-emitting efficiency of green-light device is increased by 6%-14%,and the light-emitting efficiency of red-light device is increased by5%-15%. Therefore, the compounds in the present disclosure may haveexcellent light extraction ability when being used as capping layermaterials, and may effectively improve the light-emitting efficiency ofthe OLED device.

Compared with Ref2, Ref3, and Ref4, M001, M029, M032, and M192 in thepresent disclosure may improve the refractive indices of the cappinglayer for the blue-light, green-light, and red-light wavelength regionsmerely by replacing carbon atoms with nitrogen atoms, therebyeffectively improving the blue-light, green-light and red-lightlight-emitting efficiency of the OLED device. Further, the synthesis ofthe nitrogen heterocycle may be simple, and the cost may be low, whichmay be suitable for mass production.

The description of the disclosed embodiments is provided to illustratethe present disclosure to those skilled in the art. Variousmodifications to these embodiments will be readily apparent to thoseskilled in the art, and the generic principles defined herein may beapplied to other embodiments without departing from the spirit or scopeof the disclosure. Thus, the present disclosure is not intended to belimited to the embodiments illustrated herein but is to be accorded thewidest scope consistent with the principles and novel features disclosedherein.

What is claimed is:
 1. A heterocyclic compound containing heteroatomsubstituted fluorene, the heterocyclic compound comprising a structurein Formula I:

wherein Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅,X₆, X₇ and X₈ is a N atom, and rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.
 2. Theheterocyclic compound according to claim 1, wherein: any one, two, orthree of X₁, X₂, X₃, X₄, X₅, X₆, X₇, and X₈ are a N atom, and the restare CR₂; and R₂ is selected from H, D, F, Cl, Br, a cyano group, or atrifluoromethyl group.
 3. The heterocyclic compound according to claim1, wherein: the heteroatom substituted fluorene in Formula I includesany one of following structures:

wherein Y is selected from O or S, and each of the above structures isconnected to L₁ through any carbon atom.
 4. The heterocyclic compoundaccording to claim 1, wherein: the heteroatom substituted fluorene inFormula I includes any one of following structures:

wherein Y is selected from O or S, and each of the above structures isconnected to L₁ through any carbon atom.
 5. The heterocyclic compoundaccording to claim 1, wherein: the heteroatom substituted fluorene inFormula I includes any one of following structures:

wherein Y is selected from O or S, and each of the above structures isconnected to L₁ through any carbon atom.
 6. The heterocyclic compoundaccording to claim 1, wherein: the heteroatom substituted fluorene inFormula I includes any one of following structures:

wherein Y is selected from O or S, and each of the above structures isconnected to L₁ through any carbon atom.
 7. The heterocyclic compoundaccording to claim 1, wherein: the heterocyclic compound includes anyone of following structures:


8. The heterocyclic compound according to claim 1, wherein: the L₁, L₂,and L₃ are independently selected from substituted or unsubstitutedaromatic groups.
 9. The heterocyclic compound according to claim 8,wherein: the L₁, L₂, and L₃ are independently selected from phenylene,biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene,pyrenylene, fluoranthene, triphenylene, or fluorenylene.
 10. Theheterocyclic compound according to claim 8, wherein: the L₁, L₂, and L₃are independently selected from any one of following structures:

wherein # represents a connection position.
 11. The heterocycliccompound according to claim 1, wherein: the Ar₁ and Ar₂ areindependently selected from phenyl, biphenyl, terphenyl, naphthyl,anthracenyl, phenanthryl, pyrenyl, fluoranthene, triphenylene,fluorenyl, pyrrolyl, furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl,triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl,oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, benzoxazolyl,benzothiazolyl, imidazolyl, pyrazolyl, indolyl, quinolinyl,isoquinolinyl, purinyl, isoxazolyl, isothiazole, pyrone, pyrazinyl,thienofuranyl, thienopyrrolyl, pyrrolopyridyl, pyridopyrimidinyl,pyrazolooxazolyl, pyrazinopyridazinyl, imidazothiazolyl, or coumarin.12. The heterocyclic compound according to claim 1, wherein: the Ar₁ andAr₂ are independently selected from any one of following structures:

wherein # represents a connection position.
 13. The heterocycliccompound according to claim 1, wherein: the heterocyclic compoundincludes any one of following structures:


14. A display panel, comprising: an organic light-emitting device,wherein: the organic light-emitting device includes an anode, a cathode,and an organic thin layer disposed between the anode and the cathode,and the cathode is covered with a capping layer, and the capping layerincludes any one or a combination of at least two of heterocycliccompounds, each heterocyclic compound comprising a structure in FormulaI:

wherein Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅,X₆, X₇ and X₈ is a N atom, and rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.
 15. Thedisplay panel according to claim 14, wherein: the organic thin layerincludes a hole transport layer, and the hole transport layer includesany one or a combination of the at least two of heterocyclic compounds,each heterocyclic compound comprising the structure in Formula I:

wherein Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅,X₆, X₇ and X₈ is a N atom, and the rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.
 16. Thedisplay panel according to claim 14, wherein: the organic thin layerincludes an electron blocking layer, and the electron blocking layerincludes any one or a combination of the at least two of theheterocyclic compounds, each heterocyclic compound comprising thestructure in Formula I:

wherein Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅,X₆, X₇ and X₈ is a N atom, and the rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.
 17. A displaydevice, comprising: a display panel, the display panel including anorganic light-emitting device, wherein: the organic light-emittingdevice includes an anode, a cathode, and an organic thin layer disposedbetween the anode and the cathode, and the cathode is covered with acapping layer, and the capping layer includes any one or a combinationof at least two of heterocyclic compounds, each heterocyclic compoundcomprising a structure in Formula I:

wherein Y is selected from O or S; at least one of X₁, X₂, X₃, X₄, X₅,X₆, X₇ and X₈ is a N atom, and rest are CR₂; L₁, L₂, and L₃ areindependently selected from single bond, substituted or unsubstitutedaromatic groups; Ar₁ and Ar₂ are independently selected from substitutedor unsubstituted aromatic groups or heteroaryl groups; R₁ is selectedfrom a hydrogen atom, a deuterium atom, or an aromatic group or aheteroaryl group condensed with adjacent groups; and R₂ is selected froma hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C5alkyl group, a halogen, a cyano group, or an amino group.